5-epi-β-vetivone, represented by Formula (1) below:
is a potentially valuable fragrance component due to its vetivert, woody, grapefruit aroma. Similarly, the mixture of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one, represented by Formula (3) below
and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one, represented by Formula (4) below
is a potentially valuable fragrance component as well, due to its vetivert, woody, grapefruit aroma.
One method of producing 5-epi-β-vetivone has been developed to date (11). In this process 5-epi-β-vetivone was made as a byproduct during the diastereoselective 1,4-addition of a methyl group to a double bond to synthesize (−)-solavetivone (5). However, 5-epi-β-vetivone is made as a byproduct and the disclosed process is not suitable for commercial grade production of 5-epi-β-vetivone.
No methods of producing 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one (3) and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one (4) are known to date.
Therefore, there is a current need in the art for methods to produce 5-epi-β-vetivone (1) in a fewer number of reaction steps, with higher overall yield, and from less expensive and more available starting materials. Furthermore, there is a current need in the art for methods to produce 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one (3) and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one (4).
Accordingly, the present invention is directed to novel methods for production of 5-epi-β-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one (3) and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one (4), which are useful for their fragrant qualities.